Acanthoside B

Base Information

• Chemical Name: Acanthoside B
• CAS No.: 7374-79-0
• Molecular Formula: C₂₈H₃₆O₁₃
• Molecular Weight: 580.586
• Hs Code.: 1302199099
• DSSTox Substance ID: DTXSID10994623
• Nikkaji Number: J292.920A
• Wikidata: Q27103792
• Metabolomics Workbench ID: 51784
• ChEMBL ID: CHEMBL1077080
• Mol file: 7374-79-0.mol

Synonyms:acanthoside B

Chemical Property of Acanthoside B

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.63E-25mmHg at 25°C
• Melting Point: 182-183 °C
• Refractive Index: 1.6
• Boiling Point: 778.5 °C at 760 mmHg
• PKA: 9.85±0.40(Predicted)
• Flash Point: 424.6 °C
• PSA: 174.99000
• Density: 1.399 g/cm³
• LogP: 0.68050
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 9
• Exact Mass: 580.21559120
• Heavy Atom Count: 41
• Complexity: 807

Purity/Quality:

0.8%, ^*data from raw suppliers

EleutherosideE1 >98%,StandardReferencesGrade ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C2C3COC(C3CO2)C4=CC(=C(C(=C4)OC)OC5C(C(C(C(O5)CO)O)O)O)OC
• Isomeric SMILES: COC1=CC(=CC(=C1O)OC)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C(=C4)OC)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)OC
• Description: Acanthoside B is a natural product found in Strychnos axillaris, Dalbergia sissoo, and other organisms with data available.
• Uses: Acanthoside B is mainly used for content determination and pharmacological experimental research.
• Biological Functions: Acanthoside B is an active ingredient extracted from the roots and rhizomes of Acanthopanax senticosus, which can invigorate yang and replenish qi and regulate body functions.

Technology Process of Acanthoside B

There total 4 articles about Acanthoside B which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

Acetic acid 4-{(1S,3aR,4S,6aR)-4-[3,5-dimethoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-tetrahydro-furo[3,4-c]furan-1-yl}-2,6-dimethoxy-phenyl ester (7436-67-1,137037-74-2) → (+/-)-Singaresinol-4'-O-β-D-monoglucoside (7374-79-0,137038-13-2)

Guidance literature:

With sodium methylate; In methanol; pH 10;

DOI:10.1016/S0031-9422(00)98258-X

Reference yield:

trans-sinapyl alcohol (20675-96-1) → (+/-)-Singaresinol-4'-O-β-D-monoglucoside (7374-79-0,137038-13-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / CuSO₄, air / H₂O / 48 h / 25 °C / Irradiation

2: 51 percent / 2.5 percent KOH / acetone / 1.) 0 deg C, 1.5 h, 2.) 5 deg C, overnight

3: pyridine

4: 87 percent / 1 M NaOMe / methanol / pH 10

With pyridine; potassium hydroxide; air; sodium methylate; copper(II) sulfate; In methanol; water; acetone;

DOI:10.1016/S0031-9422(00)98258-X

Reference yield:

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3,5-dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-yl]-2,6-dimethoxy-phenoxy}-tetrahydro-pyran-3-yl ester (136985-16-5,137037-73-1) → (+/-)-Singaresinol-4'-O-β-D-monoglucoside (7374-79-0,137038-13-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: 87 percent / 1 M NaOMe / methanol / pH 10

With pyridine; sodium methylate; In methanol;

DOI:10.1016/S0031-9422(00)98258-X

upstream raw materials:

Acetic acid 4-{(1S,3aR,4S,6aR)-4-[3,5-dimethoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-tetrahydro-furo[3,4-c]furan-1-yl}-2,6-dimethoxy-phenyl ester

trans-sinapyl alcohol

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3,5-dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-yl]-2,6-dimethoxy-phenoxy}-tetrahydro-pyran-3-yl ester

(+/-)-syringaresinol

Downstream raw materials:

icariside E₇

syringaresinol

(+)-syringaresinol

(+)-syringaresinol-O-β-D-glucopyranoside peracetylated

Refernces